2-Indolecarboxylic acid

It is believed [1135,1136] that the decomposition of metal complexes of salicyaldoxime and related ligands is not initiated by scission of the coordination bond M—L, but by cleavage of another bond (L—L) in the chelate ring which has been weakened on M—L bond formation. Decomposition temperatures and values of E, measured by several non-isothermal methods were obtained for the compounds M(L—L)2 where M = Cu(II), Ni(II) or Co(II) and (L—L) = salicylaldoxime. There was parallel behaviour between the thermal stability of the solid and of the complex in solution, i.e. Co < Ni < Cu. A similar parallel did not occur when (L—L) = 2-indolecarboxylic acid, and reasons for the difference are discussed... 

C9H7N03 5-hydroxy-2-indolecarboxylic acid 21598-06-1 25.00 1.3061 2 16216 C9H803 3-acetylbenzoic acid 586-42-5 25.00 1.2467 2... 

The simple 2-indolecarboxylic acid (137) and 1-carbazolecarboxylic acid (138) inhibit parathyroid hormone stimulated bone resorption . A new class of calcium ion channel activators is FPL 64176 (139) <93JMC2739>, and nitropyrrole (140) is related to the potassium ion channel activator cromakalin and has smooth muscle relaxant properties <92BMC1595>. Pyrrole (141) is a reversible potassium ion competitive inhibitor of the gastric H /K -ATPase . Ali-... 

Much improved yields (56-91%) of 3-indolone 20 were obtained when aryl substituted 3-indolecarboxylic acids 19 were subjected to these radical oxidative conditions. However, the treatment of 2-indolecarboxylic acids under identical reaction conditions gave poor yields of the corresponding 2-indolone. 

Indole-2-carboxylic acid, 5-bromo-l-hydroxy-tautomerism, 4, 197-198 Indolecarboxylic acid chloride synthesis, 4, 288... 

Eaton RW, PJ Chapman (1995) Eormation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids. J Bacteriol 177 6983-6988. 

Parallel with the developments in the benzamide area, progress was also made in several nonbenzamide series of compounds. MDL 72222 (26) [20], atropine ester of 3,5-dichlorobenzoic acid, was the first selective 5-HT3 receptor antagonist and a potent antagonist of cisplatin-induced emesis in the ferret [21]. ICS 205-930 (27) [22,23 ], the tropine ester of 3-indolecarboxylic acid, exhibited similar pharmacological and antiemetic profiles. 

There does not appear to be the same difference in ease of hydrolysis of the indolylcarboxy-lic esters and it has been recorded that ethyl indole-3-carboxylate is cleaved, via the initial hydrolysis of the ester, to give indole under both mildly acidic and alkaline conditions <72HC(25-1)1>. The effect of copper powder and of copper salts upon the decarboxylation of indolecarboxylic acids has been reviewed <72HC(25-l)227>. 

Indole-2-carboxylic acid, 3-methyl-ethyl ester chlorination, 4, 215 Indolecarboxylic acids decarboxylation, 4, 286 esterification, 4, 287 Indole-2-carboxylic acids esters... 

Intramolecular acylations of pyrrole and indolecarboxylic acids have also been effected. Compound 6b was obtained from a reaction of /3-(l-pyrrolyl)butyric acid (13a) using polyphosphoric acid (PPA) as a catalyst. No yield was given but the analogous cyclization of /3-(l-pyrrolyl)glutaric acid (13b) gave 75% of the pyrrolizinone (6c).12... 

The Darzens reaction of isatin with ethyl chloroacetate yields glycidic esters. Alkaline hydrolysis of the glycidic esters yields indole-2,3-dicarboxylic and indole-3-carboxylic acids in a 6 1 proportion. The isolation of two isomeric glycidic esters, and the fact that both produce the indolecarboxylic acids in the same proportion led to a mechanistic proposal for the formation of the later through a common intermediate439 (Scheme 101). 

Kb initio MO and DFT calculations at several levels of theory revealed a marked effect of the medium on the ionization sites of pyrrole- and indolecarboxylic acids, showing that (1) pyrrole- and indole-3-carboxylic acids behave as NH acids in the gas phase, (2) in the gas phase, pyrrole- and indole-2-carboxylic acids are deprotonated at the COOH group, although competing ionizations may take place, and (3) all these acids behave in aqueous solution as OH acids <1998JA13224>. 

A new, water soluble palladium catalyst was used in the Sonogashira reaction (Pd(OAc)2 triphenylphosphine-trisulfonate sodium salt) [131], and several groups adapted the Sonogashira coupling and subsequent cyclization to the solid-phase synthesis of indoles. Bedeschi and coworkers used this method to prepare a series of 2-substituted-5-indolecarboxylic acids [132], CoUini and Ellingboe extended the technique to l,2,3-trisubstituted-6-indolecarboxylic acids [133]. Zhang and... 

In addition to the several early examples cited by Brown [4], Scheme 2 illustrates some applications of the Reissert indole synthesis. Attempts by Beer and colleagues to improve the decarboxylation step in their synthesis of 5-hydroxyindole (equation 2) were unsuccessful, but these workers were able to synthesize 6- and 7-hydroxyindole via a Reissert method [5]. Uhle described an excellent preparation of 4-chloroindole (equation 2) [6], and Singer and Shive synthesized 7-indolecarboxylic acid (equation 3) [7] and 5-indolecarboxylic acid (equation 4) [8] via a Reissert strategy. As seen, both cyanation steps resulted in decarboxylation and cyanide replacement prior to nitrile... 

Waltman et al. [191] have attempted to polymerize electrochemically indole (Fig. 6) and its substituted derivatives. Indole, 5-cyanoindole, and 5-indolecarboxylic acid produce thick, brittle films with conductivities around 10" S cm". Thin, passivating films are formed when monomers of 4-, 6-, or 7-methylindole and 5-bromo-, 5-chloro-, or 5-fluoroindole are used. Although the structures of the polymers are not well known, infrared spectra seem to indicate the formation of N-N linkages in the polymers, which would contribute to the low observed conductivities [192]. 

Holden K.G. Antiinflammatory indolecarboxylic acid and pyridazinoindo-lecarboxylie aeid eompounds . - PCTInt. Appl US 361177, A1 19711228, 4 pp. 

Holden K.G. Antiinflanimatoiy indolecarboxylic acid and pyridazinoindo-lecarboxylic acid compounds . - PCT Int. Appl US 3519592, A1 19700707,4 pp. 

The cyclocondensation of 3-aminopyrido[3,4-h]indole (1090) and EMME in boiling acetic acid and propionic acid for 8 hr or 4 hr gave pyrimido[2, 1 6,1 ]pyrido[3,4-b]indolecarboxylate(1091) in52%and65% yields, respectively [87MIP4, 87MIP5 881JC(B)484]. 

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